Thionyl Chloride → HCID 66643628, compound

HRID 1923506Notes

Reaction equation

HRID 1923506 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:11]([CH2:12]O)=[CH:10][O:9][N:8]=1.S(Cl)([Cl:16])=O>C(Cl)Cl>[Cl:16][CH2:12][C:11]1[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[N:8][O:9][CH:10]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 66643571(3-Pyridin-2-yl-isoxazol-4-yl)-methanol

Product 1

HCID 66643628HCID 66643628, compoundYield 102.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-pyridin-2-yl-isoxazol-4-yl)-methanol (3.0 g, 16 mmol) in DCM (30 mL) at 0° C. was added thionyl chloride (3.75 g, 32 mmol) and the resulting mixture stirred for 1 h and then evaporated. After 1 h the reaction mixture was quenched with a solution of sodium hydrogen carbonate (1 N, 15 mL) and extracted with ethyl acetate. The combined extracts were washed with water, dried over sodium sulfate, filtered and concentrated to give the title compound (3.2 g, 96%) as a grey solid. MS: m/e=195.1 [M+H]+.

Workup

  1. customevaporated
  2. customAfter 1 h the reaction mixture was quenched with a solution of sodium hydrogen carbonate (1 N, 15 mL)
  3. extractionextracted with ethyl acetate
  4. washThe combined extracts were washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-46daaee0febe41dcb0444a1526309de9
Source dataset
uspto-grants-2012_05
Patent number
US08178522B2

Reaction notes

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